From the endless paperwork (co-pays, prescription refills, insurance claims!) to the stress of finding and booking an appointment with the appropriate doctor, anything healthcare-related is often—to put it simply—a headache. But does it have to be this way?

Thanks to Sherpaa, maybe not. Co-founded by Cheryl Swirnow and Dr. Jay Parkinson MD, MPH in 2012, Sherpaa, which has raised more than $5 million in funding to date, aims to make healthcare painless.

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Here's how it works: When you sign up and log into Sherpaa, you get 24/7 access to board certified female doctors, who are equipped to handle any medical or mental health concern. Meaning, if you wake up with a worrisome symptom (and we've all been there)— be it a rash, pain, or some other troublesome thing—instead of calling your doctor or G-chatting your best friend, you can take a picture and/or describe the issue in a text or e-mail. The doctor on duty will immediately diagnose your issue and, if necessary, prescribe you medicine. And if she feels as if the symptom warrants some IRL attention, she will schedule you in with a doctor or specialist ASAP. Sherpaa's staff can also renew prescriptions directly, which will save you a doctor's visit (and co-pay).

In case you need any more convincing, Sherpaa has a team of insurance guides who will go over your medical bills and explain and highlight errors. Now if only someone could create an equally comprehensive online dating service, the Internet would be complete:

If you could only follow five people on Twitter who would they be?

Greatest piece of advice you've ever been given?

To give myself a break, literally and figuratively. I try to find pockets in the day to take time out, whether that's a morning workout, walk around the block at noon, or playing with my son before dinner. I also cut myself some slack on trying to "do it all." I do the best that I can every day, in every area of my life, and I don't beat myself up about things.

What would you tell your 16-year-old self?

None of the idiots you are dating now are going to hold a candle to your handsome husband.

What was your biggest mistake?

I've certainly made some decisions in life that later turned out to be not as great as expected, but I can't say I regret anything. Every "mistake" has led me to where I am today. For example: Sherpaa ended up terminating a relationship with a lucrative client because their administrator (and our main point of contact) was rude and disrespectful to members of our team. This was early in our company's history, and we worried we made a mistake by ending the relationship. In the end, this was for the best: Our internal team respected Jay and me for backing them up and putting them above the bottom line, and future investors saw this as an example of the type of founders we are.

What was the last book you read?

The Goldfinch by Donna Tartt.

Someone gives you a crystal ball that lets you look five years into the future; what do you see?

I see my family, healthy and happy, and I see Sherpaa continuing to grow as a business and continuing to effect change in the way that businesses view healthcare.